Hydroalumination of 3-butyn-1-ol: Application to a stereoselective synthesis of (3E,5Z)-3,5-dodecadienyl acetate, the sex pheromone of the leaf roller moth
Pheromone 1 may be prepared highly stereoselectively with hydroalumination of 3-butyn-1-ol as a key step.
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Synthesis of E-vinyl iodides via Pd-catalyzed hydrostannation of terminal alkynes
2012, TetrahedronCitation Excerpt :Other reagents were purchased from Sigma–Aldrich and used without further purification. 10-Undecyn-1-ol 1b was prepared by bromination/dehydrobromination of 10-undecen-1-ol,33 commercially-unavailable propargylic alcohols were prepared by addition of lithium trimethylsilylacetylide to the appropriate aldehyde followed by treatment with K2CO3/MeOH.34,35 Pd2dba3 (65.0 mg, 0.147 mmol), tricyclohexylphosphonium tetrafluoroborate (99.0 mg, 0.294 mmol), and i-Pr2NEt (76.0 mg, 0.588 mmol) were added successively to CH2Cl2 (300 mL) and the resulting mixture was stirred at rt for 15 min.
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